1959 - By this time Aperture had run many non-portal related side tests including:
-Unknown experiment involving time travel
-Using a invisible laser to turn blood into gasoline
-Unknown experiment that caused humans to excrete coal
-Using nanobots to alter RNA in a attempt to remove tumors
-Pointing a superconductor at full blast at a person to try to give them superpowers
-Implanting a microchip into a person's brain for a unknown reason(known to overheat)
-Using florescent calcium to track neuronal activity in the brain, could harden and vitrify the brain
-Splicing preying mantis DNA into humans creating mantis men, a later test revolved around killing said mantis men

1979 - By this time Aperture had done more non-portal related side tests including:
-Turning a person's blood into peanut water
-Unknown experiment involving a Combataton arena
-Teleportation experiment that could result in your skin getting taken off
-Using jet engines to bring a person's water count from 60% down to 20/30%
-Unknown experiment involving taking someone apart, putting science stuff in them, then putting them back together, also included tumor removal

Early 90's - Aperture's BYDTWD ends in unspecified disaster, and the BYDTWD part of labs abandoned. Chell is around 10 at this time.http://i1142.photobucket.com/albums/...2_bts40001.jpg (Banner is made of dot matrix pritner paper which fell out of use in the early 90's)

Several days before May 16 200X - Glados is fitted with morality core to prevent hostility. Aperture hosts its Bring-Your-Cat-To-Work-Day, Glados uses BYCTWD as a way to get around her core, murders scientists, and assumes control of facility. By this time Aperture has access to the modern portal gun, HEV suits and chargers, health chargers, turrets, and what looks to be a Grav-gun. Chell is around 20 and is put into cryo-stasis till Portal 1http://www.thinkwithportals.com/comic/http://www.thinkwithportals.com/comic/#14 (Apertures many devices are featured in the largest panel)

Sometime After Portal 1 - Events of Portal 2. The announcer at beginning gives the total suspension time as 99999 but does not give a specific reference to it being days, months or years. However the announcer is broken so the number of days/months/years it says you were in suspension is very likely wrong.

*note* The combine takeover of earth had to have occurred SHORTLY after HL1, at most a year later. The reason being that in HL2 due to suppression device, preventing reproduction, everyone appears to be at least 20+ years old meaning the Seven hour war had to occur shortly After HL1. The combine would have needed this time to set up the suppression field quickly enough as to explain everyone's age in HL after the nearly 20 year time gaphttp://half-life.wikia.com/wiki/Suppression_Field

1986-200X - Modern Aperture Science facility built, work on Glados begins and Caroline is put inside Glados, due to hostility the AI has to be shut down frequently.

Awesome, but one oversight. Old Aperture wasn't sealed with Cave's death. The Borealis, built by Aperture, was signed and developed by GLaDOS and it ended up down there in connection with one of Cave's old teleportation experiments.

Also, I'm not sure you can judge decay in a stasis chamber as reasonable proof of passage of time. The things are made to store humans that are just sitting on the bed indefinitely.

Why does the general design of everything (buttons, boxes, etc.) in the modern test-chambers look different from Portal 1? GladOS was offline the whole time. Also Wheatly uses old chambers from her that she must have made before Portal 1 yet they have the new design

Isn't Portal 2 many years after Portal? Meaning it can't be during the events of Half Life 2 and its episodes.

Edit: That's actually one of the things that was faintly disappointing. There was mention of a disaster that had happened on Earth, but it would have been pretty cool if there was a small remark about the Combine or something. The Black Mesa mention from Cave Johnstone was good enough I guess.

As for the modern stuff looking different then in portal 1 its possible that the Personality spheres besides Wheatly continued advancing science and when Glados woke up she downloaded their data and used it herself or it may be a simple Retcon of the image basically you suppose to assume the things in portal 1 looked the way they did in Portal 2.

Portal 2 can take place during the events of HL2, Hl1 happened in 200x, the combine invasion happened right after that maybe not even a year and Portal 1 was confirmed to take place right after the combine invasion. The announcer at the begining of Portal 2 says you have been asleep for 9999 days hitting its max counter. 9999 days is about 27 years putting portal 2 right after HL2 which is said to be slightly over 20 years after HL1.

As for the modern stuff looking different then in portal 1 its possible that the Personality spheres besides Wheatly continued advancing science and when Glados woke up she downloaded their data and used it herself or it may be a simple Retcon of the image basically you suppose to assume the things in portal 1 looked the way they did in Portal 2.

Portal 2 can take place during the events of HL2, Hl1 happened in 200x, the combine invasion happened right after that maybe not even a year and Portal 1 was confirmed to take place right after the combine invasion. The announcer at the begining of Portal 2 says you have been asleep for 9999 days hitting its max counter. 9999 days is about 27 years putting portal 2 right after HL2 which is said to be slightly over 20 years after HL1.

Correct me if I'm wrong - but I believe in Cave gets the engineers working on the technology to transfer his mind into a computer right away, aka when he was still alive. It just wasn't finished when he died, and hence, he wanted Caroline to be put in his place.

actually the announcer doesn't say days or years have just looked it up he just says 9999 then static then 9999 again

Cave did start the mind data thing in 1986 as evidenced by his prerecord message in the conversion gel test chamber who has a wall with the date 1986 on it.
he died later in 1986. Cave said that he wanted Caroline to run the place and to put her brain the computer should he die so she can run the place. however its never stated when the mind scan tech was finished and Glados as a computer had been around since at least 1971ish when it signed for the Borealis blueprints.
Caroline would have been the defacto leader of Aperture till the mind scan tech was finished and that could have happened anywhere from 1986 to 200X when Glados was turned on for bring your daughter to work day.

The announcer at the begining of Portal 2 says you have been asleep for 9999 days hitting its max counter. 9999 days is about 27 years putting portal 2 right after HL2 which is said to be slightly over 20 years after HL1.

Just because it reached its max counter doesn't mean you've been asleep for exactly 9999 days... Also for the record he says 9999999, and yes I just brought the game back up to confirm that. Like others just said, when you wake up the second time around he just says 9999999, and you never hear him say days or years. I said it once and I'll say it again, it has been confirmed by VALVe staff that Portal 2 takes place CENTURIES after the first game.

Isn't Portal 2 many years after Portal? Meaning it can't be during the events of Half Life 2 and its episodes.

Edit: That's actually one of the things that was faintly disappointing. There was mention of a disaster that had happened on Earth, but it would have been pretty cool if there was a small remark about the Combine or something. The Black Mesa mention from Cave Johnstone was good enough I guess.

the announcer says nine, nine, nine, and starts a fourth nine before being cut off, so 9999/365=27.39452054794521 that's now long Chell was under, hl2 is 202X so its possible its at the same time, but i think the bring your daughter to work day happens before 200x.